Bioorganic & Medicinal Chemistry 2012-01-15

Ultrasound mediated catalyst free synthesis of 6H-1-benzopyrano[4,3-b]quinolin-6-ones leading to novel quinoline derivatives: their evaluation as potential anti-cancer agents.

Naveen Mulakayala, D Rambabu, Mohan Rao Raja, Chaitanya M, Chitta Suresh Kumar, Arunasree M Kalle, G Rama Krishna, C Malla Reddy, M V Basaveswara Rao, Manojit Pal

Index: Bioorg. Med. Chem. 20 , 759-68, (2012)

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Abstract

A facile and catalyst free synthesis of 6H-1-benzopyrano[4,3-b]quinolin-6-ones has been accomplished via the reaction of 4-chloro-2-oxo-2H-chromene-3-carbaldehyde with various aromatic amines in the presence of ultrasound. Some of these compounds were converted to the corresponding 2-(3-(hydroxymethyl)quinolin-2-yl)phenols and further structure elaboration of a representative quinoline derivative is presented. Molecular structure of two representative compounds was confirmed by single crystal X-ray diffraction study. Many of these compounds were evaluated for their anti-proliferative properties in vitro against four cancer cell lines and several compounds were found to be active. Further in vitro studies indicated that inhibition of sirtuins could be the possible mechanism of action of these molecules.Copyright © 2011 Elsevier Ltd. All rights reserved.